Zeolite-promoted selective mono-N-methylation of aniline with dimethyl carbonate

Esakkidurai, Thirugnanasamy; Pitchumani, Kasi

doi:10.1016/j.molcata.2004.03.047

Cited by 9 publications

(3 citation statements)

References 30 publications

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“…1-(4-(Methylamino)phenyl)ethanone (1), 18 N,2-dimethylbenzenamine (5c), 47,48 2,2,2-trifluoro-N-o-tolylacetamide (6b), 49 N-methyl-N-o-tolylacetamide (6c), 50 4-bromoacetyl-N,N-dimethylbenzeneamine (11), 18 5-bromo-3-iodopyridin-2-amine (7i), 51 2-amino-5-bromonicotinonitrile (7j), 20 IMPY (12a), 15 desmethyl-IMPY (14d), 18 and PIB (2-(4′-methylaminophenyl)-6-hydroxybenzothiazole) 14 were synthesized as reported. [ 3 H]PIB ([N-methyl-3 H 3 ]-2-(4′-methylaminophenyl)-6-hydroxybenzothiazole, 80 Ci per mmol) was obtained from GE Healthcare (www.customlabelling.com).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure−Affinity Relationships of New 4-(6-Iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine Derivatives as Ligands for Human β-Amyloid Plaques

et al. 2007

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A new and extensive set of 4-(6-iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine (IMPY) derivatives was synthesized and assayed for affinity toward human Abeta plaques. 6-Ethylthio- (12h), 6-cyano- (12e), 6-nitro- (12f), and 6-p-methoxybenzylthio- (15d) analogues were discovered to have high affinity (KI < 10 nM). However, introduction of a hydrophilic thioether group in the 6-position (15a-c, 15e-g) reduced or abolished affinity. In secondary N-methyl analogues, a bromo substituent in the adjacent ring position (14a) imparted high affinity (KI = 7.4 nM) whereas a methyl substituent did not (14c). The tolerance for nonhydrophilic thioether substituents in the 6-position opens up the possibility of developing new sensitive positron emission tomography radioligands for imaging human Abeta plaques in Alzheimer's disease, especially in view of the amenability of thioethers to be labeled with carbon-11 or fluorine-18 through S-alkylation reactions. The structure-activity relationships revealed in this study extends insight into the topography of the binding site for IMPY-like ligands in human Abeta plaques.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Structure−Affinity Relationships of New 4-(6-Iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine Derivatives as Ligands for Human β-Amyloid Plaques

et al. 2007

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“…As the zeolites exhibited effective catalytic activity to the methylation reaction of some aromatic amines [16,17,[22][23][24], several different zeolites such as H , H-ZSM-5, NaX, NaY, and MCM-41 were chosen to catalyze the reaction of MDA with DMC in order to obtain MBDMA, as shown in Table 1. Disparate catalytic performances were observed.…”

Section: Catalyst Functionmentioning

confidence: 99%

Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)

Qiu

Wang²,

et al. 2018

Journal of Chemistry

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The full N,N-methylation of 4,4 -methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4 -methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190 ∘ C for 6 h. The catalyst could be used for two more times with acceptable MBDMA yields higher than 90%. The main by-products were identified as three N-methylated derivatives. Surprisingly, the formation of the N-methoxycarbonylation product was extremely restrained, which could be produced in high yields of 98% on zinc acetate catalyst. Furthermore, the reaction pathway to the major product MBDMA was proposed. Finally, a feasible synthetic route of 4,4 -methylene bis(N,N-dimethylaniline) (MBDMA) was established, featuring a high yield, mild reaction conditions, and simple operations.

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“…Thus, alkylanilines formed the basic raw materials for synthesis of organic chemicals and chemical intermediates or additives in dyes, fuel oil, synthetic rubbers, explosives, herbicides, and pharmaceuticals [1][2][3][4][5]. The reaction involving the alkylation of aniline (PhNH 2 ) with base alcohol (MeOH, EtOH) had been previously studied using several different kinds of catalysts such as zeolites [6,7], composites [8][9][10][11][12][13][14][15], and clays [4]. However, all of the reactions catalyzed by these materials were carried out at higher temperature (200-400 • C), higher pressure, longer procedure, moreover, the catalysts used for the alkylation of aniline must be calcined.…”

Section: Introductionmentioning

confidence: 99%

A novel electrochemical alkylation of aniline with methanol over Zn/Cu salts modified kaolin

Ma¹,

Wang²,

Zhao³

2008

Journal of Hazardous Materials

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Zeolite-promoted selective mono-N-methylation of aniline with dimethyl carbonate

Cited by 9 publications

References 30 publications

Synthesis and Structure−Affinity Relationships of New 4-(6-Iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine Derivatives as Ligands for Human β-Amyloid Plaques

Synthesis and Structure−Affinity Relationships of New 4-(6-Iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-dimethylbenzeneamine Derivatives as Ligands for Human β-Amyloid Plaques

Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)

A novel electrochemical alkylation of aniline with methanol over Zn/Cu salts modified kaolin

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